2-Methoxyestradiol

Source: Wikipedia, the free encyclopedia.

Not to be confused with 2-Methoxyestriol.
2-Methoxyestradiol
Clinical data
Trade namesPanzem
Other names2-ME2; 2-MeO-E2; 2-MeOE2; 2-Hydroxyestradiol 2-methyl ether; 2-Methoxyestra-1,3,5(10)-triene-3,17β-diol
Identifiers
  • (8R,9S,13S,14S,17S)-2-Methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
JSmol)
SMILES
  • Oc1cc3c(cc1OC)[C@H]2CC[C@@]4([C@@H](O)CC[C@H]4[C@@H]2CC3)C
  • InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1 checkY
  • Key:CQOQDQWUFQDJMK-SSTWWWIQSA-N checkY
 ☒NcheckY (what is this?)  (verify)

2-Methoxyestradiol (2-ME2, 2-MeO-E2) is a

G protein-coupled estrogen receptor (GPER) (10 nM, relative to 3–6 nM for estradiol).[5][6]

Selected biological properties of endogenous estrogens in rats
Estrogen
RBA
Tooltip relative binding affinity (%)		 Uterine weight (%)
Uterotrophy
 LHTooltip Luteinizing hormone levels (%)
RBA
Tooltip relative binding affinity (%)
Control – 100 – 100 –
Estradiol (E2) 100 506 ± 20 +++ 12–19 100
Estrone (E1) 11 ± 8 490 ± 22 +++ ? 20
Estriol (E3) 10 ± 4 468 ± 30 +++ 8–18 3
Estetrol (E4) 0.5 ± 0.2 ? Inactive ? 1
17α-Estradiol 4.2 ± 0.8 ? ? ? ?
2-Hydroxyestradiol 24 ± 7 285 ± 8 +b 31–61 28
2-Methoxyestradiol 0.05 ± 0.04 101 Inactive ? 130
4-Hydroxyestradiol 45 ± 12 ? ? ? ?
4-Methoxyestradiol 1.3 ± 0.2 260 ++ ? 9
4-Fluoroestradiola 180 ± 43 ? +++ ? ?
2-Hydroxyestrone 1.9 ± 0.8 130 ± 9 Inactive 110–142 8
2-Methoxyestrone 0.01 ± 0.00 103 ± 7 Inactive 95–100 120
4-Hydroxyestrone 11 ± 4 351 ++ 21–50 35
4-Methoxyestrone 0.13 ± 0.04 338 ++ 65–92 12
16α-Hydroxyestrone 2.8 ± 1.0 552 ± 42 +++ 7–24 <0.5
2-Hydroxyestriol 0.9 ± 0.3 302 +b ? ?
2-Methoxyestriol 0.01 ± 0.00 ? Inactive ? 4
Notes: Values are mean ± SD or range. ER RBA =
endogenous
). b = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours). Sources: See template.

Clinical development

2-Methoxyestradiol was being

clinical trials against breast cancer.[8] A phase II trial of 18 advanced ovarian cancer patients reported encouraging results in October 2007.[9]

Preclinical models also suggest that 2-methoxyestradiol could also be effective against

microtubule inhibitor[10] and is inhibitory against prostate cancer in rodents.[11]

As of 2015[update], all clinical development of 2-methoxyestradiol has been suspended or discontinued.

sulfamate ester of 2-methoxyestradiol.[13]

Clinical effects

2-Methoxyestradiol was found to increase sex hormone-binding globulin (SHBG) levels in men by 2.5-fold at a dose of 400 mg/day and by 4-fold at a dose of 1,200 mg/day.[14] Conversely, it did not seem to suppress testosterone levels.[14]

A study in 2000 indicated that 2-Methoxyestradiol induces G2/M cycle arrest,

autoimmune thyroid disease in women.[15]

See also

References

  1. S2CID 20055299
    .
  2. PMID 22366193
    .
  3. PMID 12543804
    .
  4. PMID 12586754
    .
  5. PMID 26023144
    .
  6. PMID 26585123
    .
  7. ^ "EntreMed's Statistics". EntreMed, Inc. Archived from the original on May 4, 2005.
  8. PMID 19228747
    .
  9. ^ "EntreMed Presents Results for Panzem NCD Phase 2 Ovarian Cancer Study". Archived from the original on July 17, 2012.
  10. S2CID 1541302
    .
  11. PMID 16229806
    .
  12. ^ "2-Methoxyestradiol - CASI Pharmaceuticals". Adis Insight. Springer Nature Switzerland AG. Retrieved 2 March 2017.
  13. ^
    PMID 29618488
    .
  14. ^
    PMID 16166441
    .
  15. PMID 10940494
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=2-Methoxyestradiol&oldid=1279810751"